Hydrochloric Acid → 5-(2-pyrazinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochloride

HRID 12814Notes

Reaction equation

HRID 12814 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[C:8](=[O:33])[NH:9][C:10](=[O:32])[N:11]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][C@H:20]3[C@:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)([CH2:19]3)[CH2:17]2)[CH:12]=1.[ClH:34]>O1CCOCC1>[ClH:34].[ClH:34].[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[C:8](=[O:33])[NH:9][C:10](=[O:32])[N:11]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][C@H:20]3[C@:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=4)([CH2:19]3)[CH2:17]2)[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 247582255-(2-pyrazinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 686916625-(2-pyrazinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-(2-pyrazinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione (E67, 78 mg, 0.17 mmol) was dissolved in 2 ml of dioxane and then 4N HCl in dioxane solution (85 μl, 0.34 mmol) was added. The mixture was stirred at room temperature for 5 minutes, and then the solvent was removed in vacuum. The residue was triturated with petroleum ether to give 81.2 mg of the title compound as a yellow solid (90%, yield).

Workup

  1. customthe solvent was removed in vacuum
  2. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-f48e8a8551c445d5bdf134ee8428d15a
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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